Portable digital media players have become popular in recent years, because of their small size and ability to enable users to access digital media files on the go. Users typically store most or all of their digital media collections on personal computers, which have large storage capacities, and store only a portion of their digital media collections on portable media players, since these devices tend to have smaller storage capacities than personal computers. As a result, synchronization programs have been developed that assist users in managing the process of selecting and transferring media files between a personal computer and a portable media players.
However, current synchronization programs suffer from the drawback that in some situations they do not provide a user with sufficient information for the user to efficiently manage the synchronization process. For example, during a file transfer operation, current synchronization programs do not offer the user sufficient feedback regarding whether the portable media player has sufficient storage capacity to accommodate the transfer of selected files. As a result, the user may not be able to complete a desired file transfer, and/or may have difficulty in selecting files to delete on the portable media player in order to make room for the file transfer.